Is it safe to say that someone looking for buy and hold rental properties would be less concerned with timing the market versus finding good cash flowing deals and dollar cost averaging into the market as it cycles? 

I understand the principle but in almost every case, the property was bought for $X, was immidiately worth $X + 15%, then a mere 6 months later there majically appeared an incremental 20% property value increase.

I can understand a lender not wanting to get into a third position as the LTV increases. 

As of  Jan 1st 2019 I have raised the rent for both of the 1 bedrooms from $625/month to $685 One of the tenants did balk but they paid it because that is still under value by about $50-60 The garage rent has been raised to $140 from $100 The renter of the garage made no issue of the rent increase.

It really is best to be on both to increase your exposure.

The obvious thought is to not claim any as it is my first property and there will be only around $4k in revenue this year anyway but my thought is that I can potentially claim and increase my taxable income which will raise my Debt/Equity ratio in order to purchase another SFH or small MFH next year.

I am not going to increase by more than $20 per year. 

That being said if you're projecting out you should also consider whatever market rent is since increasing rents to that figure may offset the tax increase. 

I feel comfortable about the location/price however am concerned about the general contractor part of things.

This concerns me because I know a newbie can get under water fast with this strategy.